8

In Empire Strikes Back Cloud City is shown to be a mining colony for tibanna gas, and that's it.

However, in most books that refer to Cloud City, they mention that it is a resort and casino city. When did this first start?

6

New canon references appear to be introduced in these properties:

Star Wars, Absolutely Everything You Need to Know (reference)

Lando (comic)

Empire's End (novel)

http://starwars.wikia.com/wiki/Cloud_City/

In terms of Legends era - as far as "official" - StarWars.com referenced gambling on Cloud City in 1999:

Additionally, further back, there seem to be several references in West End RPG materials:

http://starwars.wikia.com/wiki/A_Guide_to_the_Star_Wars_Universe - 1984

http://starwars.wikia.com/wiki/Crisis_on_Cloud_City - 1989

http://starwars.wikia.com/wiki/Galaxy_Guide_2:_Yavin_and_Bespin - 1989

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